Decety and Lamm argued that empathy is “the ability to experience and understand what others feel without confusion between oneself and others” (italics added; 2006, p. 1146). Excessive identification with another who is suffering appears to lead to personal distress and avoidance rather than empathic concern. This is particularly a problem for roles involving helping or other forms of emotional labour. And yet there is a potential paradox here as empathy appears to be motivated by a felt sense of connection between self and other. How can we understand self-other differentiation in a way that allows us to improve it in organisations? In this chapter I present a contextual, behavioural approach that explains why mindfulness programs work to improve self-other differentiation. We can see self and other either in terms of a) conceptualisations, b) a flow of experiences or c) as awareness itself. Responding to conceptualisations of self and other can be helpful but can also impair empathy. Self-other differentiation at the level of content generally creates separation and judgement rather than empathy. Responding at the level of present-moment experience is the essence of responding to the others experience but it is here that differentiation of self and other is essential for mature, sustainable empathy. At the level of awareness itself, a stable sense of self beyond threat can be contacted in such a way to support empathy. Furthermore, in rare instances one can experience a sense of shared awareness that transcends difference. Mindfulness training appears to support the development of all three senses of perspective taking in a way that can enhance empathy, but also improve organisational outcomes in other areas such as authentic leadership.

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